There are a handful of key branding milestones in Cindy’s career as a supermodel: the Pepsi ads, the workout tape and the swimsuit calendar. In this clip, we go on location for her calendar shoot in Cabo San Lucas with Marco Glaviano (photographer), Ronnie Stam (hair), and Carol Shaw (makeup), and get a peek behind the scenes. Cindy is as unaffected as ever. She recounts the dietary restrictions of prepping for a swimsuit shoot and complains good naturedly about the heat. She quips that one of the bottoms is way too tiny and pointedly remarks that a swimsuit that looks cheap in real life can photograph beautifully. Cindy also takes a moment to distinguish the different responsibilities of a shoot that she herself commissions versus a regular paid gig. Half of the calendar's proceeds went to fund leukemia research; today, copies can fetch anywhere from $50-$100 on eBay.

The photographs are pretty T&A-heavy. There are a lot of suggestive poses—“backshots” with thongs that generously feature Cindy’s posterior; seriously small bikinis; a topless denim look; and some see-through mesh one-pieces. Cindy’s hair is flipped in a deep side part and tousled with a little saltwater crunch. It’s funny because by this point in the show you know Cindy’s face well enough that you can watch it transform from her regular, talking, House of Style face to her "model" face.

This is also one of the moments where you recall how major Cindy was. Girl is insanely hardbody. Sure, she's thin but it's her muscle tone in those hiiiiiiiiigh-cut late-’80s-early-’90s bathing suit bottoms that's mind-blowing. You can’t really compare it to the musculature of any working model today. It's Sports Illustrated swimsuit issue-esque but even more... honed.

The reason why this shoot is a big deal is because the calendar is such a savvy business move. It recognizes how fickle the high-fashion industry is by broadening her appeal exponentially. Even amongst supermodels, this is what makes Cindy exceptional: She knows that hanging in the back office of a garage or the wall of a college kid's dorm does not preclude selling the romance of a $30,000 evening gown. It’s not about getting bullied by an d-bag photographer and pushy stylist on the set of a men’s magazine shoot. This is a multiple-page advertisement for Cindy by Cindy. “For this kind of thing, because it’s my project, it’s my calendar… I want to see the Polaroids,” she says. “We don’t shoot until Marco and I have agreed that we both think it looks good.” The images are timeless. Marco explains, “I believe that this type of photography, even though they may seem simple now and pin-up-y or whatever, years from now they’re going to weather and age better than the other pictures we do, which are maybe more artistic.”

Helena is sort of like Claudia Schiffer, in that it feels weird to have ever had to introduce the Danish supermodel to fashion fans. For a lot of us, she rolled into our lives in the black-and-white Herb Ritts music video for Chris Isaak’s multiplatinum “Wicked Game.” In it Helena appears near-naked and writhes around in the sand with a super sprung Isaak. The imagery is bewitching and the chemistry bonkers. “She walked up on the set and our eyes made contact,” remembers Isaak. “It was like there was an open book: Everybody read it and said, 'There is a magnetism between these people.'" The three-day shoot in Hawaii came after Helena modeled in Paris for two years, but before that, the 5’ 10” beauty was huge on the pageant circuit. Helena Christensen was crowned Miss Denmark and went on to represent her country at the 1986 Miss Universe pageant.

In fact, if you break down all the supermodels’ CVs and pedigrees, it’s like they’ve been engineered by a secret society of master eugenicists. Being the hot girl in a major video and being a beauty queen is cool but she's also a master linguist. “A model from South America taught me Spanish,” she says. “When you’re from Denmark, you learn a lot of languages because no one speaks Danish. You learn English, German, French. And then I speak Swedish because I’ve got lots of Swedish friends and it’s quite similar. It’s great to be able to speak languages in this business.” She'd also go on to become a respected photographer, open a store in the West Village (Butik), and be appointed creative director of Nylon magazine. No. Big. Deal.

Helena seems appealing and approachable here. She talks about her love of vintage clothing (her mother owned a vintage clothing store in Denmark) and looks unpolished. Whether it’s a post-beauty queen grunge period or her youth, Helena wears simple clothes, looks a wee bit wan and has mussed hair. She looks unkempt and totally badass.

We’re in Milan to see what goes into a model fitting there. Cindy tries on Dolce & Gabbana’s Spring ’93 collection, and the Italian duo feature more of the long, lean, lithe, Brit-rock-gone-hippie looks that were popular that season. We're talking floppy hats, clogs, chunky heels, peasant blouses, maxi skirts, chokers, patchwork, and massive ’70s collars. There’s even a bit where the girls dress up in matching, shrunken mod suits like the Beatles in the early Brian Epstein years. Linda Evangelista, with her perfectly bobbed hair, plays John Lennon, and is slightly embarrassed by the prospect of fake-playing a guitar.

Cindy talks about the process: finding your rack, going through all the adjustments, having your Polaroid taken for reference so you know how the pieces go together and what accessories go where (this was the year, after all, when everyone wore gobs of necklaces, gold rings, massive cameos, hats, feathers and scarves) and how her assignment—number 11—sets her order in the show. She jokingly remarks that she’s been bumped down from having opened the show last year.

Cindy introduces us to Domenico Dolce and Stefano Gabbana, and then sits down with them as a journalist to discuss their inspiration for the season and their shared appreciation of breasts—their favorite body part on a lady. It’s amusing to note that Carla Bruni is wearing a replica of the Queen’s crown given that she’s since been First Lady of France. But it’s a beret-wearing Madonna, with overly plucked eyebrows and perfectly in-sync circle Lennon glasses, jumping onstage for the encore that steals the show. Asked about her presence, Madge simply replies that she and the designers are friends. The collection is sprawling and stunning, and it’s lovely for us to see a runway show in the time before livestreaming and backstage cams from this many vantage points.

We’re at Fashion Week after hours with Naomi Campbell, Linda Evangelista, and Kristen McMenamy. The three striking women are visibly fatigued after a long day of fittings and shows, and we get a genuine, loopy vibe from them that gives this behind-the-scenes footage a sense of honesty. They’re just too beat to put up veils. Not that Naomi has ever had any problems being herself, but seeing three supermodels sitting on the floor of a hotel bathroom (a very nice hotel bathroom, mind you) holding up chicken cutlet boob inserts and commenting about their lack of “tits” is remarkably engaging.

After Linda goes home, Kristen and Naomi play dress-up. Naomi puts on a dress that cost her $15 with a $10 poncho. Kristen models a number of her characteristically gothy black dresses, and then Naomi shows off her one-of-a-kind purple suedeAnna Sui ensemble. Kristen leaves (only after jumping all over Naomi’s enormous bed), and then Naomi begins her nighttime ablutions. She’s wearing an oversized tie-dyed tee as she washes her face and exfoliates. It’s an intimate, memorable moment not only because she muses about her future husband, but also because, when she’s traded all her pretty togs for a night shirt and no makeup, she looks very much the young girl that she is. Then she does something awesome: Without any self-consciousness about being on national television, she applies zit cream to her face with a Q-Tip: “I’ve got zits so I’m going to put my spots cream on and I don’t care. Everybody has zits.” It’s humanizing and feels impossibly far away from the Naomi we know today, what with the phone-throwing tantrums and diva behavior.

Photographer Mario Testino goes on a rainy day photo shoot in Milan in 1992.Photo: MTV

Street photography is nothing new now, what with the proliferation of work from Scott Schuman (The Sartorialist) and Tommy Ton (Jak & Jil) and every subsequent riff on the theme, but it’s interesting to see how legendary fashion photographer Mario Testino shot scenes from Milan. First of all, we can’t neglect to mention how beautifully dressed the photographer is, in an impeccably layered, unmistakably Italian ensemble: French cuffs, a jolt of color in his cardigan, a tartan umbrella and a navy blazer with an ASCOT. It’s everything you’d see in a GQgallery of the Italian trade show Pitti Uomo today (though I appreciate that Pitti happens in Firenze).

Testino talks about how much he loves shooting architecture in black and white (accompanied by the requisite shots of the Duomo), but he also talks about how much he loves shooting details like messy electrical wiring above a storefront. The end results are unfussy and lovely. Testino describes how much he loves taking photos of children and older people when he’s shooting for pleasure, adding that older generations have all the style. It’s an admirable quirk for an artist renowned for capturing the most beautiful supermodels of the time, but he’s not alone in this sentiment. Check out Ari Seth Cohen’s Advanced Style blog, that features chic women in their 80s and 90s. It's fabulous... As is Mario’s admirably thick head of hair.

Designer Stephen Sprouse returns to fashion with a collection shot for 'Harper's Bazaar' in 1992.Photo: MTV

On hiatus since December 1988, the artist, photographer and designer Stephen Sprouse returned to fashion with “CyberPunk,” a 32-piece capsule collection made exclusively for Bergdorf Goodman. After a shoulder injury forced a switch to shoes with Velcro fastenings and a commission from Axl Rose of Guns N’ Roses to create tour outfits, Sprouse decided to create a line of androgynous clothing that exclusively featured Velcro closures. To commemorate the occasion, the designer shot a fashion editorial for Harper’s Bazaar.

To give you a little background as to the significance of Sprouse’s return to fashion, you must first know that he was an important figure in the downtown New York scene. He made clothes for his neighbor Debbie Harry; he collaborated with Andy Warhol, creating prints with the artist’s camo silkscreens. Sprouse also worked with Keith Haring, who designed his signature “squibbles” for a number of garments in Sprouse’s 1983 collection. However, the younger generation may better remember Sprouse’s Day-Glo graffiti hand style from the 2008 Marc Jacobs Louis Vuitton ads shot by Terry Richardson, where the designer appears naked with a “defaced” LV monogram weekender hiding his privates. The 2008 collection of “It Bags” were actually an homage to the collaboration between Marc and Steven in 2000, before the artist passed away due to heart failure in 2004.

In a Harper’s Bazaar article in 2008, Jacobs said of Sprouse, “He had this desire to take what he saw in the streets and elevate it. He was using all this stuff that was so costly, really beautiful materials, and he was doing it all so beautifully. There are so many people who try to affect a street style, but it doesn't have the integrity. Stephen's work was so stylistic, and it had street cred.”

Sprouse abandoned fashion to focus on his art career, but resumed making clothes for two collections. CyberPunk’s least expensive piece was a pair of men’s undergarments that retailed for $500, but it’s the luxe ponchos, floor-length hooded tunics, military detailing and post-apocalyptic armor plating that are notable for their fit and dramatic flair: streetwear gone wildly couture.

If you’ve never flipped through Kevyn’s books— The Art of Makeup, Making Faces and Face Forward, which show transformations of regular people into historical figures or turn Hollywood stars into… other Hollywood stars—you absolutely should. Before your favorite YouTube makeup artist showed off step-by-step instructions on how to turn herself into Jared Leto or Justin Bieber, there was Kevyn Aucoin (who died of organ failure, caused by an addiction to the prescription painkillers he took for a pituitary tumor), turning Martha Stewart into Veronica Lake and Christina Ricci into Edith Piaf. Kevyn had a featured column in Allure and was one of the most celebrated makeup artists of his day.

In this segment, Kevyn (along with makeup artist Carol Shaw) teaches us how to pluck our eyebrows. Or, rather, how to overpluck them, since this was the early ’90s, when a pencil-thin arch and a lip-lined pout were all the rage. It’s the video version of the magazine illustration that always told you to take a pencil and point it towards your nose and make sure your nostril and the fat part of the brow met at a certain angle. However, the best advice comes from Carol Shaw, who tells us to use a white nail pencil (a device that helped whiten French manicure tips—another beauty casualty of the decade) to mark where you wanted to pluck, and to use a stiff, angled brush and eyeshadow to fill in the brow and finish the look.

Cindy and a Fredro Starr-less Onyx go grocery shopping at a health food store. This is a segment created to educate college kids about nutrition so that they can avoid gaining the 15-20 pounds that we all inevitably gain that first year because class feels entirely optional and eating a chimichanga at 4 AM seemed like a good idea at the time. There are interstitials, with nutritionist Jennifer Stack, advising us against believing claims made on the front of pre-packaged food, and advising viewers to refer to the side panel for concrete nutritional information. Stack also suggests eating dry cereal as a snack, and seeking out pre-washed, pre-cut vegetables. It’s all pretty straightforward and ’90s. So, like, circa when everybody ate carbs.

Cindy and Onyx eat Fig Newtons because they have zero fat (ahem: despite the sugar content). At one point, Sticky Fingaz mentions that the store’s Corn Flakes and Cheerios are fake: They’re the small-box organic kind called “Oatios” that you often see at stores that feature juice bars. On that topic, Cindy drags Suavé, Sticky and the late Big DS to try shots of wheatgrass juice. Despite all the health benefits, the three pass on doing the shot and fake Cindy out, who drinks hers. While I understand that the segment is designed to appeal to college-aged teens by touting a healthy message from their favorite rappers, the piece feels disjointed. These guys could care less about fondling gourds at the health food store. The highlight is when Cindy blots Sticky Fingaz’s T-zone. It’s very stage mom in the best way.

Fall 1993 is just like every other season since time immemorial in that white shirts are a big deal. These white shirts feature hints of the ’60s and ’70s: billowing, off-the-shoulder poet blouses with exaggerated, pointy collars that harken back to polyester leisure suits. French cuffs were also huge, as was layered suiting. This was a season for white shirts with vests; and suit-weight, sleeveless dresses with thick straps worn over them. We run the gamut from tunic-length tops with belts and a harlequin shirt from Dolce & Gabbana that features a massive Elizabethan ruff (on the lovely Kate Moss) from the other collection they design, Complice. We see offerings from Byron Lars, Rifat Ozbek, Atsuro Tayamo, Chanel, and Todd Oldham: They’re accessible and easy to mimic, and the key here is understanding how each shirt is styled and how the different silhouettes and design features are accentuated to create a high-fashion twist on a staple.

Designer and 'House of Style' correspondent Todd Oldham makes accessories for less than $1.98 in 1993.Photo: MTV

It’s both laudable and laughable that House of Style gave Todd a budget of $2.00 to remix a fall wardrobe. It’s sort of like Rachael’s Ray’s “40 Dollars a Day,” in which she barely leaves a tip and never, EVER has a cocktail, because the $1.98 does not include things like whole sweaters, boots, and a hacksaw. What it does include is a slew of Sharpies, embroidery thread, beets (yup, like the kind for borscht) and a great deal of pluck and adorable ingenuity.

This particular “Todd Time” feels like we’re playing a practical joke on him, and to his credit, he creates some fascinating fashion and does lay groundwork for some ideas that you can apply to pretty much any item of clothing. There is a patchwork sweater created out of 5 other sweaters (that this fits the $1.98 budget is totally lol); given how huge patchwork was as a trend in the ’90s, it’s not a bad idea. Cutting up ill-fitting or moth-eaten sweaters in large pieces (the key being to cut an entire chest section and part of an armscye so that you don’t actually have to construct a sweater out of small swatches) and sewing them together in a large, looping, visible stitches creates a sort of frankensweater that you can at the very least guarantee no one else will have. An errant piece with arms makes a giant, floppy beanie that sort of looks like those tie-top Triple 5 Soul hats. A hacksaw applied to a pair of boots creates a rather "bless-its-heart" looking, peep-toe-boot-flip-flop situation, and bisected beets dye pink polka dots onto an old striped button-down. Sharpie squiggles finish off the look, and the whole thing is plunged into salted water for the vegetable dye to set. A backpack gets zipper pulls made out of twigs. For your efforts, the end result evokes a very crafty hobo.

The entire back-to-school episode feels very much like a teen magazine except that here we get to see real professionals bringing the lessons to life with moving images. Makeup artist Carol Shaw holds our hand and walks us through a series of small, manageable info nuggets on how to apply different cosmetics. Carol is also the founder of the makeup company Lorac (“Carol” backwards) that’s still popular today, but her tips are wholly product agnostic.

Carol suggests fragrance-free products, and instructs us on how to bend the wand of a new tube of Maybelline Great Lash so that you can pile it on with more accuracy. She also advises us to smile while applying blush so that we know where it goes; she recommends light coverage on foundation because in that case (unlike mascara), less is more. She tells us that moisturizer, cleanser and toner are all you need for a skin-care regimen, as most of us already know. The one thing she teaches that’s a true boon is how to use foundation to lighten lipstick colors, and how to use the back of your hand like a painter’s mixing palette to create the hue you want. This way you can create an entire gradient of browns, peaches, pinks and reds from a single tube. Definitely handy advice for a college kid on a budget.

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